4-(2-Methyl­anilino)pent-3-en-2-one

Venter, G.J.S.; Steyl, G.; Roodt, A.

doi:10.1107/S1600536810021045

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Pages o1593-o1594

doi:10.1107/S1600536810021045

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4-(2-Methylanilino)pent-3-en-2-one

Gertruida J. S. Venter,^a ^* Gideon Steyl ^a and Andreas Roodt ^a

^aDepartment of Chemistry, University of the Free State, PO Box 339, Bloemfontein 9300, South Africa
^*Correspondence e-mail: truidie@hotmail.com

(Received 3 May 2010; accepted 2 June 2010; online 5 June 2010)

The title enamino ketone, C₁₂H₁₅NO, a derivative of 4-(phenylamino)pent-3-en-2-one, presents a roughly planar [greatest displacement of an atom from the pentenone plane is 0.033 (2) Å] pentenone backbone, enhanced by an intramolecular N—H⋯O hydrogen bond; the asymmetry in C—C distances in the group suggests the presence of unsaturated bonds. The overall geometry in the free ligand differs significantly from that in other reported compounds, in which it is coordinated to rhodium; this is reflected in the bond distances [the N⋯O distance is significantly increased (0.2 Å) upon coordination to the metal] and the dihedral angle between the benzene ring and the pentenone backbone [49.53 (5)°]. All of the methyl goups are rotationally disordered over two orientations of equal occupancy.

Related literature

For synthetic background, see: Shaheen et al. (2006 ). For applications of enaminoketones in liquid crystals, see: Pyżuk et al. (1993 ), in fluorescence, see: Xia et al. (2008 ), in complexes of medical interest, see: Tan et al. (2008 ); Chen & Rhodes (1996 ), in catalysis, see: Nair et al. (2002 ); Van Aswegen et al. (1991 ); Steyn et al. (1992 , 1997 ); Otto et al. (1998 ); Roodt & Steyn (2000 ); Brink et al. (2010 ). For the structures of related ligand systems, see: Damoense et al. (1994 ); Venter et al. (2009a ,b ).

Experimental

Crystal data

C₁₂H₁₅NO
M_r = 189.25
Monoclinic, P 2₁ /c
a = 7.5674 (7) Å
b = 11.5075 (9) Å
c = 12.0996 (11) Å
β = 92.154 (5)°
V = 1052.91 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.55 × 0.23 × 0.12 mm

Data collection

Bruker X8 APEXII 4K Kappa CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.960, T_max = 0.991
10022 measured reflections
2308 independent reflections
1854 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.150
S = 1.07
2308 reflections
129 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N11—H11⋯O12	0.91	1.90	2.6345 (19)	136

Table 2
Comparative geometrical parameters (Å, °) for free and coordinated N,O-bidendate (N,O-bid) compounds

Parameters	(I)	(II)	(III)	(IV)
C111—N11	1.422 (2)	1.521 (4)/1.463 (3)	1.440 (4)	-
C2—N11	1.345 (2)	1.320 (4)	1.319 (4)	1.303 (6)
C4—O12	1.257 (2)	1.290 (3)	1.291 (4)	1.281 (6)
C2—C3	1.383 (3)	1.410 (4)	1.423 (4)	1.396 (7)
C3—C4	1.420 (2)	1.365 (3)	1.382 (3)	1.388 (9)
O12⋯N11	2.635 (2)	2.885 (3)	2.886 (3)	2.826 (6)
N11—C2—C4—O12	−0.5 (1)	4.1 (2)	−2.6 (2)	1.2 (4)
Dihedral angle	49.53 (5)	87.47 (4)/89.36 (8)	85.58 (8)	-
Notes: (I) This work; (II) N,O-bid = 4-(2,3-dimethyl phenylamino)pent-3-en-2-onato (Venter et al., 2009a); (III) N,O-bid = 4-(2,6-dimethyl phenylamino)pent-3-en-2-onato (Venter et al., 2009b). (IV) N,O-bid = 4-amino-pent-3-en-2-onato (Damoense et al., 1994). The dihedral angle is defined as the torsion angle between the N–C–C–C–O plane and the benzene ring. A positive angle denotes a clockwise rotation.

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810021045/bg2348sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810021045/bg2348Isup2.hkl

checkCIF report

Comment top

A well-known system in organometallic chemistry is the β-diketone compound AcacH (acetylacetone; or when coordinated acetylacetonato, acac^-). A multitude of derivatives have been synthesized to date, with enaminoketones being one type. Since enaminoketones contain nitrogen and oxygen atoms as well as an unsaturated C—C bond, these electron-rich compounds are of interest in various fields including liquid crystals [Pyżuk et al. (1993)], fluorescence studies [Xia et al. (2008)] as well as formation of complexes of medical interest [Tan et al. (2008); Chen & Rhodes (1996)]. It also has significant application possibilities in catalysis [Nair et al. (2002); Van Aswegen et al. (1991); Steyn et al. (1992; 1997); Otto et al. (1998); Roodt & Steyn (2000); Brink et al. (2010)].

The title enaminoketone is a derivative of 4-(phenylamino)pent-3-en-2-one [PhonyH; Shaheen et al. (2006)]. Fig. 1 shows a view of the molecule. The C₂–C₃ distance of 1.383 (3) Å, versus the C₃–C₄ distance of 1.420 (2)Å indicates an unsaturated bond in the pentenone backbone, which is otherwise planar, probably helped by an intramolecular N₁—H₁···O₁ bond (N₁—H_1: 0.91Å; H₁···O₁: 1.90Å; N_1···O₁:2.635 (2)Å, N₁—H₁···O: 136.4°). In general terms, the geometry in the free ligand differs significantly from that in other reported compounds where it is coordinated to rhodium [Table1; Venter et al. (2009a; 2009b); Damoense et al. (1994)]; fon instance, the N₁···O₁ distance is greatly ncreased (~0.2 Å) upon coordination to the metal, as it is the dihedral angle between the phenyl ring and the pentenone backbone. All the methyl goups appear rotationally disordered in two sites of similar occupation.

Related literature top

For synthetic background, see: Shaheen et al. (2006). For applications of enaminoketones in liquid crystals, see: Pyżuk et al. (1993), in fluorescence, see: Xia et al. (2008), in complexes of medical interest, see: Tan et al. (2008); Chen & Rhodes (1996), in catalysis, see: Nair et al. (2002); Van Aswegen et al. (1991); Steyn et al. (1992, 1997); Otto et al. (1998); Roodt & Steyn (2000); Brink et al. (2010). For the structures of related ligand systems, see: Damoense et al. (1994); Venter et al. (2009a,b).

Experimental top

A solution of acetylacetone (11.07 g, 0.1106 mol), 2-Me-aniline (10.73 g, 0.1008 mol) and 2 drops of H₂SO₄(conc.) in 150 ml benzene was refluxed for 6 hours in a DeanStark trap, filtered and left to crystallize. Crystals suitable for X-Ray diffraction were obtained in 17.86 g (94.32 %) yield. This compound is stable in air and light over a period of several months.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability displacement level.

4-(2-Methylanilino)pent-3-en-2-one top

Crystal data top

C₁₂H₁₅NO	F(000) = 408
M_r = 189.25	D_x = 1.194 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2889 reflections
a = 7.5674 (7) Å	θ = 2.7–28.2°
b = 11.5075 (9) Å	µ = 0.08 mm⁻¹
c = 12.0996 (11) Å	T = 100 K
β = 92.154 (5)°	Plate, colourless
V = 1052.91 (16) Å³	0.55 × 0.23 × 0.12 mm
Z = 4

Data collection top

Bruker X8 APEXII 4K Kappa CCD diffractometer	2308 independent reflections
Radiation source: fine-focus sealed tube	1854 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ω and ϕ scans	θ_max = 27°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −9→9
T_min = 0.960, T_max = 0.991	k = −14→12
10022 measured reflections	l = −15→15

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.150	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0654P)² + 0.9506P] where P = (F_o² + 2F_c²)/3
2308 reflections	(Δ/σ)_max < 0.001
129 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₁₂H₁₅NO	V = 1052.91 (16) Å³
M_r = 189.25	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.5674 (7) Å	µ = 0.08 mm⁻¹
b = 11.5075 (9) Å	T = 100 K
c = 12.0996 (11) Å	0.55 × 0.23 × 0.12 mm
β = 92.154 (5)°

Data collection top

Bruker X8 APEXII 4K Kappa CCD diffractometer	2308 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	1854 reflections with I > 2σ(I)
T_min = 0.960, T_max = 0.991	R_int = 0.034
10022 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.150	H-atom parameters constrained
S = 1.07	Δρ_max = 0.45 e Å⁻³
2308 reflections	Δρ_min = −0.35 e Å⁻³
129 parameters

Special details top

Experimental. The intensity data was collected on a Bruker X8 ApexII 4 K Kappa CCD diffractometer using an exposure time of 60 seconds/frame. A total of 688 frames were collected with a frame width of 0.5° covering up to θ = 28.24° with 99.1% completeness accomplished.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.4288 (3)	0.30725 (17)	0.73241 (16)	0.0212 (4)
H1A	0.4068	0.3907	0.723	0.032*	0.5
H1B	0.3886	0.2659	0.6653	0.032*	0.5
H1C	0.5557	0.2939	0.7458	0.032*	0.5
H1D	0.4939	0.243	0.6998	0.032*	0.5
H1E	0.5121	0.3678	0.7575	0.032*	0.5
H1F	0.345	0.3397	0.6769	0.032*	0.5
C2	0.3300 (2)	0.26340 (16)	0.82877 (15)	0.0172 (4)
C3	0.3410 (2)	0.14730 (15)	0.85770 (15)	0.0174 (4)
H3	0.4142	0.0982	0.8159	0.021*
C4	0.2494 (2)	0.09702 (15)	0.94616 (14)	0.0162 (4)
C5	0.2647 (3)	−0.03183 (16)	0.96633 (16)	0.0217 (4)
H5A	0.1945	−0.0532	1.0296	0.033*	0.5
H5B	0.3889	−0.0521	0.982	0.033*	0.5
H5C	0.2208	−0.0739	0.9005	0.033*	0.5
H5D	0.3417	−0.0663	0.9118	0.033*	0.5
H5E	0.1472	−0.0674	0.9594	0.033*	0.5
H5F	0.3153	−0.0456	1.0409	0.033*	0.5
C12	0.2730 (3)	0.49042 (17)	1.07167 (15)	0.0218 (4)
H12A	0.2961	0.4067	1.0685	0.033*	0.5
H12B	0.1797	0.5055	1.1238	0.033*	0.5
H12C	0.3812	0.5311	1.0964	0.033*	0.5
H12D	0.2752	0.5555	1.1239	0.033*	0.5
H12E	0.3917	0.4567	1.0687	0.033*	0.5
H12F	0.1901	0.4311	1.0961	0.033*	0.5
O12	0.15430 (17)	0.15514 (11)	1.00878 (10)	0.0195 (3)
C111	0.1994 (2)	0.45704 (15)	0.86788 (15)	0.0160 (4)
C112	0.2147 (2)	0.53330 (16)	0.95849 (15)	0.0172 (4)
C113	0.1737 (2)	0.64979 (16)	0.94050 (16)	0.0203 (4)
H113	0.1821	0.7026	1.0008	0.024*
C114	0.1207 (2)	0.69078 (16)	0.83647 (16)	0.0208 (4)
H114	0.0932	0.7707	0.8262	0.025*
C115	0.1081 (2)	0.61469 (16)	0.74784 (15)	0.0192 (4)
H115	0.0738	0.6426	0.6763	0.023*
C116	0.1456 (2)	0.49751 (16)	0.76367 (15)	0.0180 (4)
H116	0.1344	0.445	0.7032	0.022*
N11	0.2320 (2)	0.33691 (13)	0.88747 (13)	0.0176 (3)
H11	0.1801	0.3060	0.9471	0.021*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0225 (9)	0.0206 (9)	0.0210 (9)	0.0019 (7)	0.0057 (7)	0.0032 (7)
C2	0.0167 (8)	0.0190 (9)	0.0159 (9)	0.0001 (7)	0.0001 (7)	−0.0007 (7)
C3	0.0192 (9)	0.0163 (9)	0.0168 (9)	0.0028 (7)	0.0029 (7)	−0.0015 (7)
C4	0.0176 (8)	0.0157 (9)	0.0152 (8)	0.0008 (7)	−0.0013 (7)	−0.0010 (7)
C5	0.0254 (10)	0.0152 (9)	0.0250 (10)	0.0014 (7)	0.0062 (8)	0.0005 (7)
C12	0.0221 (9)	0.0244 (10)	0.0188 (9)	−0.0010 (8)	0.0000 (7)	−0.0015 (7)
O12	0.0254 (7)	0.0157 (6)	0.0176 (7)	0.0015 (5)	0.0051 (5)	−0.0001 (5)
C111	0.0158 (8)	0.0122 (8)	0.0202 (9)	−0.0008 (6)	0.0032 (7)	0.0003 (7)
C112	0.0164 (8)	0.0177 (9)	0.0177 (9)	−0.0018 (7)	0.0023 (7)	−0.0002 (7)
C113	0.0222 (9)	0.0170 (9)	0.0220 (9)	−0.0018 (7)	0.0033 (7)	−0.0059 (7)
C114	0.0214 (9)	0.0129 (8)	0.0284 (10)	0.0004 (7)	0.0047 (8)	0.0012 (7)
C115	0.0189 (9)	0.0190 (9)	0.0198 (9)	−0.0001 (7)	0.0024 (7)	0.0031 (7)
C116	0.0200 (9)	0.0163 (9)	0.0178 (9)	−0.0020 (7)	0.0020 (7)	−0.0018 (7)
N11	0.0232 (8)	0.0132 (7)	0.0168 (8)	0.0009 (6)	0.0053 (6)	0.0012 (6)

Geometric parameters (Å, º) top

C1—C2	1.496 (2)	C12—C112	1.506 (3)
C1—H1A	0.98	C12—H12A	0.98
C1—H1B	0.98	C12—H12B	0.98
C1—H1C	0.98	C12—H12C	0.98
C1—H1D	0.98	C12—H12D	0.98
C1—H1E	0.98	C12—H12E	0.98
C1—H1F	0.98	C12—H12F	0.98
C2—N11	1.345 (2)	C111—C116	1.391 (3)
C2—C3	1.383 (3)	C111—C112	1.406 (3)
C3—C4	1.420 (2)	C111—N11	1.422 (2)
C3—H3	0.95	C112—C113	1.391 (3)
C4—O12	1.257 (2)	C113—C114	1.389 (3)
C4—C5	1.506 (2)	C113—H113	0.95
C5—H5A	0.98	C114—C115	1.385 (3)
C5—H5B	0.98	C114—H114	0.95
C5—H5C	0.98	C115—C116	1.390 (3)
C5—H5D	0.98	C115—H115	0.95
C5—H5E	0.98	C116—H116	0.95
C5—H5F	0.98	N11—H11	0.9071

C2—C1—H1A	109.5	H5B—C5—H5F	56.3
C2—C1—H1B	109.5	H5C—C5—H5F	141.1
H1A—C1—H1B	109.5	H5D—C5—H5F	109.5
C2—C1—H1C	109.5	H5E—C5—H5F	109.5
H1A—C1—H1C	109.5	C112—C12—H12A	109.5
H1B—C1—H1C	109.5	C112—C12—H12B	109.5
C2—C1—H1D	109.5	H12A—C12—H12B	109.5
H1A—C1—H1D	141.1	C112—C12—H12C	109.5
H1B—C1—H1D	56.3	H12A—C12—H12C	109.5
H1C—C1—H1D	56.3	H12B—C12—H12C	109.5
C2—C1—H1E	109.5	C112—C12—H12D	109.5
H1A—C1—H1E	56.3	H12A—C12—H12D	141.1
H1B—C1—H1E	141.1	H12B—C12—H12D	56.3
H1C—C1—H1E	56.3	H12C—C12—H12D	56.3
H1D—C1—H1E	109.5	C112—C12—H12E	109.5
C2—C1—H1F	109.5	H12A—C12—H12E	56.3
H1A—C1—H1F	56.3	H12B—C12—H12E	141.1
H1B—C1—H1F	56.3	H12C—C12—H12E	56.3
H1C—C1—H1F	141.1	H12D—C12—H12E	109.5
H1D—C1—H1F	109.5	C112—C12—H12F	109.5
H1E—C1—H1F	109.5	H12A—C12—H12F	56.3
N11—C2—C3	120.21 (16)	H12B—C12—H12F	56.3
N11—C2—C1	120.06 (16)	H12C—C12—H12F	141.1
C3—C2—C1	119.73 (16)	H12D—C12—H12F	109.5
C2—C3—C4	123.91 (16)	H12E—C12—H12F	109.5
C2—C3—H3	118	C116—C111—C112	120.72 (16)
C4—C3—H3	118	C116—C111—N11	121.30 (16)
O12—C4—C3	122.97 (16)	C112—C111—N11	117.91 (16)
O12—C4—C5	117.93 (16)	C113—C112—C111	117.91 (17)
C3—C4—C5	119.10 (15)	C113—C112—C12	120.93 (16)
C4—C5—H5A	109.5	C111—C112—C12	121.16 (16)
C4—C5—H5B	109.5	C114—C113—C112	121.61 (17)
H5A—C5—H5B	109.5	C114—C113—H113	119.2
C4—C5—H5C	109.5	C112—C113—H113	119.2
H5A—C5—H5C	109.5	C115—C114—C113	119.74 (17)
H5B—C5—H5C	109.5	C115—C114—H114	120.1
C4—C5—H5D	109.5	C113—C114—H114	120.1
H5A—C5—H5D	141.1	C114—C115—C116	119.93 (17)
H5B—C5—H5D	56.3	C114—C115—H115	120
H5C—C5—H5D	56.3	C116—C115—H115	120
C4—C5—H5E	109.5	C115—C116—C111	120.08 (17)
H5A—C5—H5E	56.3	C115—C116—H116	120
H5B—C5—H5E	141.1	C111—C116—H116	120
H5C—C5—H5E	56.3	C2—N11—C111	128.22 (16)
H5D—C5—H5E	109.5	C2—N11—H11	115.9
C4—C5—H5F	109.5	C111—N11—H11	115.9
H5A—C5—H5F	56.3

N11—C2—C3—C4	1.9 (3)	C112—C113—C114—C115	−0.1 (3)
C1—C2—C3—C4	−178.62 (17)	C113—C114—C115—C116	1.1 (3)
C2—C3—C4—O12	−2.6 (3)	C114—C115—C116—C111	−1.4 (3)
C2—C3—C4—C5	177.01 (17)	C112—C111—C116—C115	0.7 (3)
C116—C111—C112—C113	0.3 (3)	N11—C111—C116—C115	177.51 (16)
N11—C111—C112—C113	−176.63 (16)	C3—C2—N11—C111	−177.32 (17)
C116—C111—C112—C12	−179.96 (16)	C1—C2—N11—C111	3.2 (3)
N11—C111—C112—C12	3.1 (3)	C116—C111—N11—C2	48.9 (3)
C111—C112—C113—C114	−0.6 (3)	C112—C111—N11—C2	−134.19 (19)
C12—C112—C113—C114	179.64 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O12	0.91	1.90	2.6345 (19)	136

Experimental details

Crystal data
Chemical formula	C₁₂H₁₅NO
M_r	189.25
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	7.5674 (7), 11.5075 (9), 12.0996 (11)
β (°)	92.154 (5)
V (Å³)	1052.91 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.55 × 0.23 × 0.12

Data collection
Diffractometer	Bruker X8 APEXII 4K Kappa CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.960, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	10022, 2308, 1854
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.150, 1.07
No. of reflections	2308
No. of parameters	129
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.35

Computer programs: APEX2 (Bruker, 2005), SAINT-Plus (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O12	0.91	1.90	2.6345 (19)	136.4

Comparative geometrical parameters (Å, °) for free and coordinated N,O-bidendate (N,O-bid) compounds top

Parameters	(I)	(II)	(III)	(IV)
N11—C111	1.422 (2)	1.521 (4)/1.463 (3)	1.440 (4)	-
N11—C2	1.345 (2)	1.320 (4)	1.319 (4)	1.303 (6)
O12—C4	1.257 (2)	1.290 (3)	1.291 (4)	1.281 (6)
C2—C3	1.383 (3)	1.410 (4)	1.423 (4)	1.396 (7)
C3—C4	1.420 (2)	1.365 (3)	1.382 (3)	1.388 (9)
N11···O12	2.635 (2)	2.885 (3)	2.886 (3)	2.826 (6)
N11—C2—C4—O12	-0.5 (1)	4.1 (2)	-2.6 (2)	1.2 (4)
Dihedral angle	49.53 (5)	87.47 (4)/89.36 (8)	85.58 (8)	-

Notes: (I) This work; (II) N,O-bid = 4-(2,3-dimethyl phenylamino)pent-3-en-2-onato (Venter et al., 2009a); (III) N,O-bid = 4-(2,6-dimethyl phenylamino)pent-3-en-2-onato (Venter et al., 2009b). (IV) N,O-bid = 4-amino-pent-3-en-2-onato (Damoense, et al., 1994).

Acknowledgements

Financial assistance from the University of the Free State is gratefully acknowledged. We also express our gratitude towards SASOL, the UFS Materials and Nanosciences Academic Cluster and the South African National Research Foundation (SA-NRF/THRIP) for financial support of this project. Part of this material is based on work supported by the SA-NRF/THRIP under grant No. GUN 2068915. Opinions, findings, conclusions or recommendations expressed in this material are those of the authors and do not necessarily reflect the views of the SA-NRF.

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